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Search results; Over 1,000 homes in Healdsburg

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Top guest favourite
Home in Healdsburg
Vineyard View Retreat • Fire Pit • Wine Perks
2 bedrooms, 3 beds, 2 private bathrooms
16–21 Nov
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4.96 out of 5 average rating, 98 reviews
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Top guest favourite
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds
8–13 Nov
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 125 reviews
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Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 queen beds
25–30 Oct
5.0 out of 5 average rating, 275 reviews
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Top guest favourite
Home in Healdsburg
Vineyard Vue - Wine Tastings Included
3 bedrooms, 3 beds
28 Oct – 2 Nov
4.99 out of 5 average rating, 76 reviews
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Guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Hideaway
2 bedrooms, 2 beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 85 reviews
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Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
3 bedrooms, 3 queen beds
25–30 Oct
4.98 out of 5 average rating, 49 reviews
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Top guest favourite
Guest house in Healdsburg
The Roost - Sun Room
1 bedroom, 1 queen bed
4–9 Oct
4.94 out of 5 average rating, 374 reviews
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Top guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 53 reviews
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Guest favourite
Home in Healdsburg
Healdsburg 2br Cottage with Private Yard!
2 bedrooms, 2 beds
4–9 Oct
4.92 out of 5 average rating, 157 reviews
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Top guest favourite
Home in Healdsburg
Wine Country Resort Home | Pool & Spa | Sleeps 12
5 bedrooms, 6 beds
15–20 Nov
4.95 out of 5 average rating, 127 reviews
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Top guest favourite
Guest house in Healdsburg
Luxurious, Private, Healdsburg Guest Cottage
1 bedroom, 1 king bed
30 Oct – 4 Nov
4.99 out of 5 average rating, 321 reviews
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Guest favourite
Villa in Healdsburg
Private Hilltop Estate · Pool · Valley Views
6 bedrooms, 5 beds
10–15 Nov
4.95 out of 5 average rating, 19 reviews
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Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
3 bedrooms, 4 beds
21–26 Sept
4.94 out of 5 average rating, 102 reviews
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Top guest favourite
Flat in Healdsburg
2 Bedroom Flat In Downtown Healdsburg
2 bedrooms, 2 beds
16–21 Nov
4.97 out of 5 average rating, 140 reviews
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Top guest favourite
Home in Healdsburg
Ivy House Healdsburg @Ivyhousehealdsburg
2 bedrooms, 2 beds
15–20 Oct
4.97 out of 5 average rating, 73 reviews
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Top guest favourite
Home in Geyserville
Luxurious Wine Country Estate
8 bedrooms, 8 beds
7–12 Oct
5.0 out of 5 average rating, 50 reviews
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Guest favourite
Home in Healdsburg
Healdsburg Plaza Gem-Hot Tub and Tastings Included
2 bedrooms, 2 queen beds
22–27 Nov
4.91 out of 5 average rating, 97 reviews
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Luxe
Home in Healdsburg
Villa with Pool, Hot Tub and Tastings Included
3 bedrooms, 3 king beds
11–16 Oct
4.98 out of 5 average rating, 64 reviews